Unified biomime+c assembly of voacalgine A and bipleiophylline via divergent oxida+ve couplings
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1 Unified biomimec assembly of voacalgine A and bipleiophylline via divergent oxidave couplings Lachkar, D.; Denizot,.; Beradat, G.; Ahamada, K.; Beniddir, M.A.; Dumontet, V.; Gallard, J.F.; Guillot, R.; Leblanc, K.; nang, E..; Turpin, V.; Kouklovsky, C.; Poupon, E.; Evanno, L.; Vincent, G. at. Chem. 2017, AP. Tim McFadden, Current Literature, 5/6/17 Tim Wipf Group Page 1 of 16 8/6/2017
2 Introduction atural Products Voacolgine A - monoindole alkaloid - isolated from voacanga grandifolia - possible biosynthec precursor to bipleiophylline - has shown moderate cell growth inhibitory effects against L- 60 and CT116 cells voacalgine A (originally assigned structure) Bipleiophylline - bisindole alkaloid with aromac spacer - isolated from Alstonia angus4folia - biological acvity not reported - synthec mountain to climb due to complexity bipleiophylline Tetrahedron, 2013, 69, rg. Le@. 2008, 10, Design and Strategy in rganic Synthesis: From the Chiron Approach to Catalysis (Wiley- VC, 2013). pleiocarpamine C 2 pyrocatechuic acid 2 Tim Wipf Group Page 2 of 16 8/6/2017
3 Introduction Biosynthesis, Strategy C 2 [] C 2 pleiocarpamine voacalgine A (originally assigned structure) biosynthetic dead-end? voacalgine A (revised structure) bipleiophylline 'western' moiety R C 2 [] R R R R 'eastern' moiety 3 Tim Wipf Group Page 3 of 16 8/6/2017
4 Western Moiety: Reaction ptimization C 2 conditions C 2 entry oxidant solvent addi=ve =me isolated yield 1 K 3 [Fe(C) 6 ] % 2 DDQ % 3 CA % 4 ai % 5 PhI(Ac) 2 DCM none 15 h 0%, but 6 Ag 2 DCM none 6 h 14% 7 Ag 2 C none 6 h trace 8 Ag 2 DCM C 2 () 40 min 38% 4 Tim Wipf Group Page 4 of 16 8/6/2017
5 Western Moiety, Diels-Alder Side Reaction C 2 C 2 PhI(Ac) 2 () DCM, rt, 15 h 2 C 55%, 1:1 via C 2 R 1 R 3 R 2 C 2 Ag 2 (5 equiv), C 2 () DCM, rt R 2 R 3 R 1 C 2 Cl C 2 C 2 C 2 38%, 40 min 18%, 90 min 19%, 90 min 5 Tim Wipf Group Page 5 of 16 8/6/2017
6 Eastern Moiety: ptimization C 2 Ag 2 (5 equiv), additive () solvent, rt, 12 h entry solvent addi=ve isolated yield 1 DCM none 10% 2 C none 51% 3 C C 2 63% 4 C 2 none 0% (decomp) 6 Tim Wipf Group Page 6 of 16 8/6/2017
7 Eastern Moiety: Scope R 1 R 3 R 2 C 2 Ag 2 (5 equiv), C 2 () C, rt, 5 12 h R 1 R 3 R 2 R 1 R 1 =, 62% R 1 =, 45% R 1 =, 64% R 1 =F, 64% R 1 =Cl, 71% R 1 =Br, 62% 67% 31% Ts 53% 62% 30% 7 Tim Wipf Group Page 7 of 16 8/6/2017
8 chanism Control Reactions R' R'' C 2 R''' Ag 2 (5 equiv), C 2 () DCM R' R'' or R'' C 2 R''' C 2 C 2 C 2 C 2 8 Tim Wipf Group Page 8 of 16 8/6/2017
9 chanism Calculations I B3LYP/6-31G* calculaons used to locate transion states Considered three reacon pathways: 1) stepwise reacon: anchoring, trapping 2) concerted, synchronous: [42], tautomerizaon 3) concerted, asynchronous: sequenal events, tautomerizaon stepwise concerted, synchronous 9 Tim Wipf Group Page 9 of 16 8/6/2017
10 chanism Calculations II concerted, asynchronous 10 Tim Wipf Group Page 10 of 16 8/6/2017
11 Increasing complexity with natural substances C 2 C 2 i) Ag 2 (5 equiv), C 2 (), C, 40 C, 12 h ii) Ag 2 (5 equiv), C 2 (solvent), rt, 8 h R C 2 yohimbine 1 equiv i) R=, 35% ii) R=, 55%, R=C, 20% geissoschizine 1 equiv C 2 Ag 2 (20 equiv) C, rt, 60 h 43% ajmalicine 1 equiv C 2 C 2 1 equiv Ag 2 (5 equiv), C 2 (solvent) rt, 16 h C 2 46% 11 Tim Wipf Group Page 11 of 16 8/6/2017
12 Double and sequential anchoring C 2 Ag 2 (5 equiv), C 2 () C, rt, 12 h 29% (1:1) Ag 2 (5 equiv), C 2 () DCM, rt, 96 h 1.5 equiv 50%, (1.6:1) C 2 C 2 Ag 2 (5 equiv), C 2 () DCM, rt, 7 d 7% C 2 C 2 ajmalicine 1.5 equiv 12 Tim Wipf Group Page 12 of 16 8/6/2017
13 Synthesis of voacalgine A, bipleiophylline C 2 - pleiocarpamine formate (0.007% from Alstonia balansae) C equiv Ag 2 (5 equiv) C, rt, 4 d 21% voacalgine A (revised structure) C 2 - Ag 2 (5 equiv), C 2 () DCM, rt, 7 d 3% (2 steps) 1. bipleiophylline 13 Tim Wipf Group Page 13 of 16 8/6/2017
14 Conclusions An oxidave coupling protocol between indole and 2,3- dihydroxybenzoic acid was developed The first syntheses of bipleiophylline and voacalgine A were achieved The structure of voacalgine A was corrected and revised 14 Tim Wipf Group Page 14 of 16 8/6/2017
15 Voacalgine A Revision voacalgine A (revised structure) 15 Tim Wipf Group Page 15 of 16 8/6/2017
16 Misc. Rxns R 1 R 3 R 2 R 4 IS R 1 R 3 R 4 R 2 via R 1 R 2 rg. Le@. 2014, 16, I R 3 Angew. Chem. Int. Ed. 2009, 48, Chem. Commun. 2015, 51, Tim Wipf Group Page 16 of 16 8/6/2017
Unified biomimetic assembly of voacalgine A and bipleiophylline via divergent oxidative couplings
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